1. Field of the Invention
The invention relates to novel oil soluble esters derived from the reaction of organic acid materials such as dicarboxylic acids or anhydrides and an aldehyde/tris-(hydroxymethyl) aminomethane adduct or mixture. These novel oil soluble esters have utility as additives for oleaginous compositions and systems including gasoline, automatic transmission fluids and libricating oils and as synthetic lubricants, per se.
2. Description of the Prior Art
Lubricant and fuel additives derived from hydrocarbon substituted succinic anhydride, e.g., polyisobutenylsuccinic anhydride, with compounds containing both an amine group and a hydroxy group have been suggested or investigated in the prior art. For example, U.S. Pat. No. 3,272,746 teaches the reaction of ethanolamine and diethanolamine, as well as various hydroxyalkyl substituted alkylene amines, such as N-(2-hydroxyethyl) ethylene diamine, N,N'-bis(2-hydroxyethyl) ethylene diamine, with alkenylsuccinic anhydride to obtain ashless dispersants for lube oil. U.S. Pat. No. 3,324,033 shows a hydroxy amine, such as diethanolamine reacted with a long chain alkenyl-succinic anhydride to form a mixture of esters and amides, wherein some of the diethanolamine reacts through a hydroxy group to give an ester linkage, while another portion of the diethanolamine forms an amide linkage. U.S. Pat. No. 3,364,001 teaches a tertiary alkanolamine reacted with an alkenylsuccinic anhydride to form an ester useful as a gasoline additive. U.S. Pat. No. 3,448,049 teaches dispersants, corrosion inhibitors and antiwear agents in lubricants and fuels by esterifying alkenylsuccinic anhydride with a hydroxy compound made by reacting an alkanolamine with an unsaturated ester, amide or nitrile. U.S. Pat. No. 3,630,904 teaches reacting a hydroxy amine, with both short and long chain dicarboxylic acid. U.S. Pat. No. 3,484,374 teaches the polymeric condensation products of polycarboxylic acid or anhydride with various alkanolamines such as aminoethyl-ethanolamine, N-methyldiethanolamine, etc. United Kingdom Specification No. 809,001 teaches corrosion inhibitors comprising a multiple salt complex derived from the reaction product of hydrocarbyl substituted dicarboxylic acids and hydroxy amines (including 2-amino-2-methyl-1,3-propane-diol [AMP] and tris hydroxy methylaminomethane (hereafter designated THAM) further complexed with mono- and polycarboxylic acids.
U.S. Pat. No. 3,756,743 teaches reacting polyisobutenylsuccinic anhydride with a polyol, such as pentaerythritol, followed by reaction with THAM. U.S. Pat. No. 3,632,511 teaches reacting polyisobutenylsuccinic anhydride with both a polyamine and a polyhydric alcohol including THAM. U.S. Pat. No. 3,679,428 teaches reacting polyisobutenylsuccinic anhydride with a mixture of pentaerythritol and THAM. United Kingdom Specification No. 984,409 teaches ashless, amide/imide/ester type lubricant additives prepared by reacting an alkenylsuccinic anhydride, with a hydroxy amine including THAM.
In British Pat. No. 564,506, the condensation product of THAM and formaldehyde, i.e. 1-aza-3,7-dioxabicyclo [3.3.0]oct-5-yl methyl alcohols is said to react with fatty acids to give unstable ester products which are useful as drying oils.
In contrast to the above disclosures, we have found that carboxylic acids or anhydrides can be treated with an aldehyde-THAM adduct or mixture to give novel compositions useful in an unusually side spectrum of additive applications.